Chemical Science, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
Intermolecular carboamination of allyl amines under Pd( ii )-catalysis is reported, expediting the synthesis vicinal diamines embedded in a functionally enriched linear carbon framework with high yields and exclusive Markovnikov selectivity.
Язык: Английский
Journal of the American Chemical Society, Год журнала: 2022, Номер 144(2), С. 648 - 661
Опубликована: Янв. 6, 2022
Nitrogen (N) is ubiquitously found in bioactive molecules, pharmaceutical agents, and organic functional materials. Accordingly, development of new C–N bond-forming catalysis has been one the long-standing research subjects synthetic chemistry. In this Perspective, recent advances highly selective amination reactions with electrophilic reagents are described: by taking advantage concept nitrogen umpolung, otherwise challenging aminofunctionalizations, such as hydroamination, aminoboration, carboamination, readily available feedstock-like alkenes alkynes possible, giving densely functionalized complex often chiral alkylamines high selectivity. The scope, limitations, reaction mechanism briefly summarized.
Язык: Английский
Процитировано
133
Journal of the American Chemical Society, Год журнала: 2023, Номер 145(25), С. 13542 - 13548
Опубликована: Июнь 12, 2023
The arylethylamine pharmacophore is conserved across a range of biologically active natural products and pharmaceuticals, particularly in molecules that act on the central nervous system. Herein, we present photoinduced copper-catalyzed azidoarylation alkenes at late stage with arylthianthrenium salts, allowing access to highly functionalized acyclic (hetero)arylethylamine scaffolds are otherwise difficult access. A mechanistic study consistent rac-BINAP-CuI-azide (2) as photoactive catalytic species. We show utility new method by expedient synthesis racemic melphalan four steps through C-H functionalization.
Язык: Английский
Процитировано
77
Journal of the American Chemical Society, Год журнала: 2023, Номер 145(30), С. 16630 - 16641
Опубликована: Июль 24, 2023
β-(Hetero)arylethylamines are privileged structural motifs found in many high-value organic molecules, including pharmaceuticals and natural products. To construct these important molecular skeletons, previous methods mainly achieved by amino(hetero)arylation reaction with the aid of transition metals preactivated substrates. Herein, we report a metal-free photoinduced intermolecular for single-step installation both (hetero)aryl iminyl groups across alkenes an efficient regioselective manner. This method shows broad scope (up to 124 examples) excellent tolerance various olefins─from simplest ethylene complex multisubstituted can all participate reaction. Furthermore, aminosulfonylation be also conducted presence sodium bisulfite as SO2 source.
Язык: Английский
Процитировано
59
Nature Chemistry, Год журнала: 2024, Номер 16(4), С. 599 - 606
Опубликована: Янв. 16, 2024
Язык: Английский
Процитировано
35
Zeitschrift für Kristallographie - New Crystal Structures, Год журнала: 2025, Номер unknown
Опубликована: Янв. 28, 2025
Abstract C 23 H 24 FeO 2 , monoclinic, P 1 / c (no. 14), a = 13.8934(19) Å, b 5.8012(7) 23.011(4) β 97.160(5)°, V 1840.2(4) Å 3 Z 4, R gt ( F ) 0.0915, w ref 0.2115, T 170 K.
Язык: Английский
Процитировано
2
ACS Catalysis, Год журнала: 2022, Номер 12(7), С. 3890 - 3896
Опубликована: Март 14, 2022
A versatile method to access differentially substituted 1,3- and 1,4-diamines via nickel-catalyzed three-component 1,2-carboamination of alkenyl amines with aryl/alkenylboronic ester nucleophiles N–O electrophiles is reported. The reaction proceeds efficiently free primary secondary without needing a directing auxiliary or protecting group enabled by fine-tuning the leaving on reagent. transformation highly regioselective compatible wide range coupling partners amine substrates, all performed at room temperature. series kinetic studies support mechanism in which alkene coordination nickel catalyst turnover-limiting.
Язык: Английский
Процитировано
39
Journal of the American Chemical Society, Год журнала: 2023, Номер 145(15), С. 8299 - 8307
Опубликована: Апрель 6, 2023
Modular strategies to rapidly increase molecular complexity have proven immensely synthetically valuable. In principle, transformation of an alkene into a dielectrophile presents opportunity deliver two unique nucleophiles across alkene. Unfortunately, the selectivity profiles known dielectrophiles largely precluded this deceptively simple synthetic approach. Herein, we demonstrate that dicationic adducts generated through electrolysis alkenes and thianthrene possess profile relative more conventional dielectrophiles. Specifically, these species undergo single perfectly regioselective substitution reaction with phthalimide salts. This observation unlocks appealing new platform for aminofunctionalization reactions. As illustrative example, implement reactivity paradigm address longstanding challenge: diamination distinct nitrogen nucleophiles. Studies mechanism process reveal key alkenyl thianthrenium salt intermediate controls exquisite regioselectivity highlight importance proton sources in controlling sulfonium electrophiles.
Язык: Английский
Процитировано
34
Synthesis, Год журнала: 2023, Номер 56(01), С. 1 - 15
Опубликована: Июнь 12, 2023
Abstract Catalytic enantioselective 1,2-dicarbofunctionalization (1,2-DCF) of alkenes is a powerful transformation growing importance in organic synthesis for constructing chiral building blocks, bioactive molecules, and agrochemicals. Both two- three-component context, this family reactions generates densely functionalized, structurally complex products single step. Across several distinct mechanistic pathways at play these transformations with nickel or palladium catalysts, stereocontrol can be obtained through tailored ligands. In Review we discuss the various strategies, mechanisms, catalysts that have been applied to achieve enantioinduction alkene 1,2-DCF. 1 Introduction 2 Two-Component Enantioselective 1,2-DCF via Migratory Insertion 3 Radical Capture 4 Three-Component 5 6 Miscellaneous Mechanisms 7 Conclusion
Язык: Английский
Процитировано
24
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(12)
Опубликована: Фев. 1, 2024
Abstract A new electrochemical transformation is presented that enables chemists to couple simple alkyl carboxylic acid derivatives with an electrophilic amine reagent construct C(sp 3 )−N bond. The success of this reaction hinges on the merging cooperative reduction nickel catalysis. chemistry exhibits a high degree practicality, showcasing its wide applicability 1°, 2°, 3° acids and remarkable compatibility diverse functional groups, even in realm late‐stage functionalization. Furthermore, extensive mechanistic studies have unveiled engagement radicals iminyl radicals; elucidated multifaceted roles played by i Pr 2 O, Ni catalyst, electricity.
Язык: Английский
Процитировано
13
Chemistry - An Asian Journal, Год журнала: 2022, Номер 17(12)
Опубликована: Апрель 23, 2022
Alkene amino(hetero)arylation presents a highly efficient and straightforward strategy for direct installation of amino groups heteroaryl rings across double bond simultaneously. An extensive array practical transformations has been developed via alkene difunctionalization approach to access broad range medicinally valuable (hetero)arylethylamine motifs. This review recent progress in 1,2-amino(hetero)arylation alkenes organized three different modes. First, intramolecular employing C, N-tethered will be introduced. Next, two-component reactions discussed with combination precursors, external aryl precursor, C-tethered amine or reagents, alkenes. Last, three-component intermolecular covered.
Язык: Английский
Процитировано
33